5-Bedroom Homes for Sale in Hillsborough, CA with Private Pool

20 Pine Court, Hillsborough A Modern Architectural Masterpiece Nestled in the prestigious Skyfarm neighborhood, 20 Pine Court is a breathtaking 5 bedroom, 5 full bath, and 2 half bath modern estate envisioned by the acclaimed Sean Bailey Design. This architectural marvel seamlessly merges sophisticated elegance with unparalleled functionality, creating a living experience that redefines luxury.

Paul Zinchik Compass

This BRAND NEW (Built in 2024) never-lived-in ECO-FRIENDLY SMART HOME blends modern sophistication with sustainable living, offering breathtaking PANORAMIC VIEWS of the San Francisco Bay. The striking exterior showcases smooth white stucco, warm wood paneling, and expansive glass elements, including a grand entrance and a three-car garage. Soaring tray ceilings, recessed & cove lighting, and

Stanley Lo Green Banker Realty

LOWER HILLSBOROUGH'S PREMIER ESTATE! Rare listing, a once-in-a-lifetime property w/ one of the LARGEST LOTS in its neighborhood -- 1.286 ACRES OF TOTALLY FLAT LAND! European style Italian Villa, constructed to perfection resembling the work of "turn-of-the-century" architect George Howard. UPDATED & RENOVATED throughout the years. EXTENSIVE STREET SETBACK. There's a Detached 5-car garage with a

Stanley Lo Green Banker Realty

Step into a piece of history w/ this extraordinary Hillsborough property, originally the 5-stall carriage house for the infamous 16-acre Fagan Estate. Transformed in 1971, the carriage house is now a luxurious single-family residence, designed to cater to modern living, while beautifully preserving the historic charm. Spanning approximately 7,000 square feet, the home includes 7 bedrooms, 4.5

Emily Patterson KW Advisors

Situated on a private side street, this grand estate sits on a majestic 2-acres with jaw-dropping panoramic bay views, some of the best in all of Hillsborough. Exquisite architectural detailing and finishes throughout, including inlaid parquet walnut floors, hand carved fireplaces, and walls of glass framing iconic bay views and landscaping. The main level includes a stunning office, billiard

Pierre & Alex Buljan Compass

Modern Luxury Meets Cozy Elegance in Burlingame Park. This NEW BUILD home effortlessly combines sleek, modern design with natural materials to create a warm, inviting atmosphere. Every corner of this masterpiece has been meticulously crafted with high-end finishes, ensuring both style and comfort.Key Features-6 Spacious Bedrooms-8 Unique Bathrooms. The heart of the home features a gourmet kitchen

Beth Taylor Coldwell Banker Realty

Perfectly situated in the heart of South Hillsborough, 280 Uplands Drive offers a rare opportunity on an expansive, flat over half-acre lot surrounded by beautiful estates. Rebuilt and remodeled approximately 35 years ago, this 5-bedroom, 4.5-bath home spans nearly 5,000 square feet and features a generous floor plan, lush landscaping, and a swimming pool. While currently owner-occupied and not

Michael Haywood Jr. eXp Realty of California Inc

In the Burlingame Country Club area, this stunning renovation combines chic sophistication with Spanish flair. Featuring 5 bedrooms and 5.5 baths across two levels, the home has espresso-hued hardwood and Saltillo tile floors complemented by updated lighting, 3 fireplaces with modern style. The floor plan features upstairs living areas and the primary suite opening to the resort-inspired rear

Alicia Sanguinetti Compass

DESIGN FOR LIVING: THE PERFECT MEETING OF SUN, CELEBRATION, AND SAVOIR FAIRE! Remodeled designer quality unfolds across multiple destinations, with minimal boundary between indoor and outdoor living. 5 bedrooms, 3 full baths, 2 half baths, plus large Office (or gym), and enormous recreation room of 21 x 26 feet. Majority of the home flows on one level, including four bedrooms all together

Geoffrey Nelson Coldwell Banker Realty

Tucked at the end of a quiet cul-de-sac on approximately 2 private acres, The Koshland Estate is a once-in-a-lifetime offering in one of the Peninsulas most prestigious enclaves. Designed in 1961 by Frank Lloyd Wright disciple Howard Friedman for his father-in-law, Levi Strauss & Co. President and CEO Daniel Koshland, the home was constructed to exceptional commercial-grade standards, rarely seen

Pierre & Alex Buljan Compass

Welcome to 760 Chateau Dr., a stunning French Tudor-style estate that exudes timeless elegance while offering an inviting and comfortable living experience on 7,285 sqft of living area. The main residence spans 5,875 sq.ft of living area across three beautifully designed levels, featuring exquisite architectural details such as a grand fleur-de-lis spiral staircase, intricate cast iron light

Eva Sogotis KW Advisors

BEST CHOICE IN ALL OF LOWER HILLSBOROUGH - PRICE REDUCED $1 MILLION!!! Welcome to 1140 Bromfield, a stunning 5-bedroom estate set on 1.11 lush acres in the prestigious Lower Hillsborough neighborhood. This meticulously crafted home blends timeless elegance with modern convenience, offering an unparalleled living experience. Inside, discover 5 full bathrooms, 2 half bathrooms, and a gourmet

Stanley Lo Green Banker Realty

NEW LISTING AND RECENTLY REFRESHED!!! ONE OF HILLSBOROUGH'S FINEST PROPERTIES!!! Breathtaking views of the San Francisco bay & beyond. HUGE MOSTLY LEVEL LOT WITH OVER .5 ACRES. Exquisite Mediterranean designs with a red-tiled roof and circular paver driveway. A grand foyer welcomes you in with soaring ceilings. Throughout, you'll find hardwood flooring, carpeting, and recessed lighting. To the

Stanley Lo Green Banker Realty